Réaction #421314

Équation de réaction

4-(2-chloro-6-morpholino-9H-purin-9-yl)-2-methylbutan-2-ol

N,N,N′,N′-tetramethylethylenediamine

n-butyllithium

hexane

1-chloro-2-iodoethane

→

4-(2-chloro-8-iodo-6-morpholino-9H-purin-9-yl)-2-methylbutan-2-ol

Rendement 78.5%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was quenched with a saturated solution of NH4Cl
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   ExtractionThe aqueous layer was extracted into ethyl acetate (3×)
4. 4
   Séchagethe combined organics were dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreabsorbed onto celite for purification by flash chromatography

Mode opératoire

A solution of 4-(2-chloro-6-morpholino-9H-purin-9-yl)-2-methylbutan-2-ol (360 mg, 1.1 mmol) and N,N,N′,N′-tetramethylethylenediamine (0.25 mL, 1.7 mmol) in THF (8.1 mL) was cooled to −42° C. and treated with a solution of 2.5M n-butyllithium in hexane (BuLi, 2.0 mL, 5.0 mmol) dropwise over 5 minutes. After 30 minutes at −42° C., 1-chloro-2-iodoethane (0.51 mL, 5.4 mmol) was added and the reaction mixture was slowly warmed to 0° C. over 1 hr. The mixture was quenched with a saturated solution of NH4Cl, and diluted with ethyl acetate. The aqueous layer was extracted into ethyl acetate (3×), and the combined organics were dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 4-(2-chloro-8-iodo-6-morpholino-9H-purin-9-yl)-2-methylbutan-2-ol as a white foam (390 mg, 78%). LC/MS (ESI+): m/z 452 (M+H)

Source